


Matchmaker, Matchmaker, Make Me a Match

by iimpish



Category: Supernatural
Genre: Alternate Universe - Modern Setting, Best Man Sam Winchester, Lawyer Sam Winchester, M/M, Matchmaker Fic, Mechanic Dean Winchester, Nervous Dean Winchester, Sassy Dean Winchester, Unimpressed!Crowley, Wedding Planning, married at first sight
Language: English
Status: In-Progress
Published: 2020-05-23
Updated: 2021-01-04
Packaged: 2021-03-03 04:08:01
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 9
Words: 19,146
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24344755
Author URL: https://archiveofourown.org/users/iimpish/pseuds/iimpish
Summary: A drunk night spent striking out on Tindr and Grindr lead Dean to fill out a questionnaire for a "unique matchmaker".
Relationships: Castiel/Dean Winchester
Comments: 39
Kudos: 105





	1. The Matchmaker

**Author's Note:**

> Inspired by the idea behind the show Married at First Sight. A work in progress that has no timetable for updates, for which I apologize. I have chapter titles figured out, if that helps? Probably not. Great big thanks to [Chaotic_Librarian](https://archiveofourown.org/users/Chaotic_Librarian) and [PrettySin](https://archiveofourown.org/users/PrettySin) for beta help and general awesomeness.

“So, Dean. Can you tell me why you decided to do this?”

How had he gotten here? He was drunk one night, flicking through Tindr and Grindr and not having any luck. One of the ads had been for a “unique matchmaker experience” and Drunk Dean thought it was a great idea. So great, in fact, that he’d stayed up until seven in the morning filling out the bajillion questions the application had asked him. Race. Height. Sex. Gender. Orientation. Religion. Eye color. Hair color. Build. Facial hair. Kink level. All of those things again, as preferences in a partner. Questions about his family, his “love language” (whatever the fuck that was), how he’d label his style of dress, hobbies, favorite songs, favorite movies, favorite TV shows, his job, where he lived, what foods he liked, his talents, his dreams, his ambitions… Deep shit for being three sheets to the wind. He supposed everything came out in a coherent manner, because the matchmaker, Pamela, had called him two days later and asked to meet him.

So here he was, in downtown Lawrence. The office of Pamela Barnes, Matchmaker, was in a tall building near the top. It was spacious and had a lot of windows letting in the sunlight. It was neutral: a lot of beige and creams, with hints of navy. The waiting room had a large sofa and some chairs, but her office held her large desk that faced the windows, and a round wooden table with only two chairs sitting at it. The chairs were comfortable, at least.

Pam was pretty. Dark hair, hazel eyes. Thin. Nice rack. She wore a white button down shirt, the top two buttons undone, and a black pencil skirt with a pair of heels. A bracelet, and Dean noticed that she didn’t wear any rings. Why was a matchmaker single?

Dean shrugged. 

The shrug, however, didn’t seem to satisfy her because her hazel eyes were boring into him and had him pinned. “I’m tired of the grind. Of going to bars and going on apps and having a meaningless fling with someone that doesn’t go anywhere. I feel like I’ve tried it all, except this.”

Pam took notes and went over every detail of his application with him again.

“What about kids?”

“What about them?”

“Do you want them?”

That made Dean stop and think for a few seconds. He played with a loose thread on his shirt, trying to find the words that said what he wanted, but didn’t make him look like an asshole, either. “No. I raised Sam. He was like havin’ my own kid, and now he’s a lawyer who I helped put through school and now it’s just. My turn.” A nod and more notes. Was she writing a book? Dean tried to read what she was writing, but her writing was tiny and pretty far away across a table, and upside down.

“What do you like to do for fun, Dean?”

“Work on my Baby. Uh, my car.”

“But you work as a mechanic? Own your own garage?”

“Yeah?” She smiled and wrote some more. “Is that bad?” He was worried now that something was wrong with him.

“Nothing’s  _ bad _ , Dean. But every detail is important when trying to find someone who you’ll be compatible with. For example, you obviously enjoy cars. So it might not be the best match to introduce you to someone who got car sick even looking at a car.”

Oh. “Yeah, that makes sense. Speaking of car sick. I don’t fly. On planes, I mean.”

Pam smiled at him. “Yes, I saw that. Any reason why?”

Dean gave another shrug. “A metal tube that weighs tens of thousands of pounds hurtling through the air five miles off the ground at 500 miles per hour. That doesn’t sound like a death trap to you?” She chuckled and made more notes.

“Tell me about your partner. Do you have a preference between male and female?”

“Not really. But, uh, I have a thing for dark hair.” It wasn’t that he discriminated. He didn’t. But if identical twins approached him and one had dark hair and one light, he’d go for the dark haired twin every day of the week.   
  
“Alright. What about height? Build?”   
  
Dean gave another shrug. “Beyond the hair, I don’t really have a ‘type’. I’ll screw anything that moves.” She may as well know that he was a man-whore. He wasn’t ashamed of it, but he was definitely getting tired of it.

They talked for hours. Kinks. Preferences. Likes. Dislikes. Hard limits. He rated his kinkiness on a scale of one to ten, and he rated his preferred kink level in a partner on the same scale. They talked about cocks and pussies and ass and tits and all of the things he’d never talked about with anyone, ever, because he was never  _ that close _ with anyone in his entire life. 

Pam asked him about his bad habits, and she knew just what to ask to get him to spill his guts even though he felt guilty saying some of the things. She asked him what were “domestic dealbreakers”, things a partner would do around the house that would make him not want to be with a person. She asked him about allergies, about pets, about favorite foods. They talked about religion and politics and how important it was to Dean that his partner shared his same views. 

“Tell me about your last three partners.”

He did. Two of the three were women. One was five foot nothing, the other five ten. One had an hourglass figure of a swimsuit model, the other was what others might call “chubby”. One was prissy and wore dresses and makeup and heels. The other liked sports, tshirts, jeans, and sneakers. The guy was shorter, about five seven, and blond. Was always eating candy and he tasted like it. Dean smiled at that memory. He’d had a lot of fun with… Um… Whatever his name was.    
  


“How long was your longest relationship, Dean?”

That took Dean a few minutes to answer. He didn’t really know. “I don’t know. A year? With Lisa.”   
  
“And when was that?” Pam asked, writing everything down still.

“When I was nineteen. Twenty.”    
  
“And you’re thirty five now?”   
  
“Yeah.”

“And you feel that you’re ready for marriage?”   
  
That caught Dean off guard a bit. Who was talking about marriage? He was looking to get more of a date than a quick fuck… “I mean. We’ll see if we click?”

Pam chuckled a little bit and smiled at him, and in Dean’s opinion, it was a bit condescending. “I’m a  _ unique _ matchmaker, Dean. Did you not read the website? The disclaimers?” He gave her a blank stare and she sighed a little, pushing away her pad and pen for the first time since he’d sat down. “I match people, and the first time they meet is when they get married, Dean. You meet at the altar. You don’t speak beforehand, you don’t know what they look like or who they are. And vice versa.”

Oh. That… Clearly he didn’t read it as thoroughly as he thought he did. Dean blinked at her, eyes wide and owlish. Pam reached across and patted his hand.

“You’re still early in the process, and we’re pretty much done here. Why don’t you take a few days and think it over? If you decide to go forward, I’ll schedule an appointment for you with a psychologist, and then get a background check done, and a full medical workup.”

“That sounds like a lot.”   
  
Pam nodded in agreement. “It is. But this isn’t just a date. I need to be sure you’re really ready for this, that you’re not a psychopath who’s going to kill someone I match you with, that you’re not going to drop dead of some sort of medical condition. If you come out the other side of all of that, then I’ll take a look at my files and see who I think you’d best fit with.”

“I’ll think about it.”   
  
“Great.” Pam slid a business card across the table to him. “Call me when you’ve made your decision. I look forward to working with you, Dean.”

★★★★

“You did what?”   
  
Dean was kind of regretting calling Sam on his way home. Now he’d never hear the end of it. “I was drunk. Lonely. Tired of the one night thing.” There was silence for a few moments, making Dean nervous. 

“Never thought I’d hear you say that.”

“What do you mean by that?”

  
He heard Sam sigh. “Nothing, Dean. Just. Since Lisa… You refuse to talk about a partner. A life beyond the garage and a quick lay. It just wasn’t on your radar or something, I guess, and I just thought it never would be.”

Dean didn’t know what to say in response, so he said nothing. 

“It’s not a bad thing, Dean.”

“So you think I should do it?” He could almost  _ see _ Sam running a hand through his hair and that made Dean smile, just a little bit.

“It’s… Unconventional. What if it doesn’t work out?”

Dean shrugged before realizing Sam couldn’t see him through the phone. “Then we divorce and go our separate ways.”

“You need a prenup. If you don’t have one, and the person is a dick, they could take half the garage, or the house.” That nearly made Dean choke. He’d worked his entire life to open his garage. He’d rather kill someone than give part of it to anyone. Sam let it sink in a bit more before speaking again. “How long until you have to decide?”

“She said to take a few days, but I guess… I mean, I guess I could take all the time I want if I wanted to go through that interrogation again.”

“That bad?”   
  
“Dude. She asked about my kinks. And what I wanted his or hers to be. And if I had a strong preference between cut and un--”

“Yeah. I got the picture. Thanks.” Dean grinned, feeling better now that he’d made his little brother uncomfortable. “Whatever you decide, you know I’ll back you, jerk.”

“Thanks, bitch.” They chatted a few more minutes and then hung up just as Dean pulled into the driveway of the little house he’d bought a couple of years ago. It was small, just enough for him and a guest room for when Sam came to visit. White with blue shutters, and a garage for Baby. He’d added the large front windows so he could see the yard when he was watching TV at night, loving the wildlife that wandered in. It was all he needed, and Dean took pride in it. It was always a relief to come home to his space, and as he walked through the door, he wondered what it’d be like to share that space with someone. Would they expect him to move in with them? Was that something they negotiated with Pam before they were matched? Maybe he should keep track of all of his questions so that he didn’t forget any for when… If. For if he decided to see her again. 

The front door opened up directly into the open layout of the house. His living room was right there and his kitchen was dead ahead. It was what the house had come with when he bought it, and while it was a hell of a lot different than the motel rooms they practically grew up in, this had become home now. Dean grabbed a beer from the fridge and retreated to his chair in front of the TV for the night. He tried not to think about whether or not he’d continue with the process with Pam, mainly because there really wasn’t any part of him that was telling him he shouldn’t do it. He already knew he was going to, but he wasn’t willing to admit that to himself just yet. 

He wondered how he was going to tell Bobby and Ellen, and how they’d react. Sure, he’d been nervous calling Sam to tell him, but it was different, somehow.

Dean spent the next few days as normally as possible. He didn’t talk to anyone about what he’d done or the decision he had to make. He didn’t even speak to Sam about it again. Every time he came into the house from being outside, he was hit with an almost overwhelming sense of emptiness. Not of himself, but of the house. It felt like there wasn’t any life in it. Up until now, he’d loved that about the house; it was his quiet sanctuary. Now, it felt all wrong.

On Tuesday at lunchtime, Dean took his phone out and dialed the number on the business card. “Pam? When can I get in to see that psychiatrist?”


	2. The Psychiatrist

**Summary for the Chapter:**

> Where Dean spills his guts.

**Notes for the Chapter:**

> Some updated tags :) I appreciate all the kudos <3

“What’s up with you, brother?”

Dean looked up with a deer-in-the-headlights look. “What?” 

Benny was wiping his hands off on one of the grease rags before closing the hood to the 1978 Lincoln Continental Mark V that he’d been working on. “You’re not paying attention, you’re not going out for drinks after work as much and when you are, you’re not hitting on everything with legs.” He said the last with a little grin telling Dean he was teasing. Kind of.   
  
“Yeah. Well.” What was he supposed to say? That he’d gotten so desperate to find someone beyond a roll in the hay that he went to a matchmaker to maybe get married to a stranger? It wasn’t like it was a sure thing. And he’d been so quiet because when he called Pam to get an appointment with this psychiatrist, there was a two week wait for an appointment so he’d been spending all of his time trying to anticipate what the appointment would be like. What questions would the doctor ask? Would he know what answers the doctor wanted to hear? Was it bad that his first instinct was to tell the doctor what they wanted to hear rather than the real, true answers? Probably. What would happen if Pam refused to match him? 

“Well what?” Benny came over and leaned against the Mustang Dean was working on, clearly not willing to let this go in the name of friendship. 

“Just a lot going on is all.” His friend snorted a little.

“Brother, you never have a lot going on. You come to work at dawn, you don’t leave until eight or nine, you either go to a bar and pick someone up or you go home and drink two beers and then repeat the next day.” 

“Harsh.” That wasn’t to say it wasn’t true. It was just painful to hear someone call him out on it like that. Benny laughed at him.

“Come on, cher. We’re goin’ out and you’re tellin’ me what’s goin’ on with you, because if don’t then as your friend I can’t figure out whether I should support you or call you an idiot.” Fair point. “We’re goin’ out tonight, brother,” he repeated after seeing Dean’s hesitation.   
  
“Benny, I really can’t, I-”   
  
“Dean, I’ve known you for ten years. I can count on one hand the number of times you didn’t go out on a Thursday or a Friday or a Saturday every week. It’s Sunday and we ain’t been out this week. Somethin’s up and we’re gonna talk about it. Beer’ll help.”

Dean gave in with a bit of a sigh. He was stuck. Benny wasn’t going to give up and Dean didn’t have any sort of good lie that his friend would believe now and forget about in a few days. “Yeah. Alright. Let me just finish the Mustang.” 

Two hours later he and Benny were in a booth at the local bar. It wasn’t a dive bar, but you wouldn’t see it on  _ Sex and the City _ , either. It was clean enough, sufficiently dark which Dean was more grateful for tonight than any other night he and Benny or other work friends had been here. The staff was friendly and knew them by now. They were usually greeted by name. There weren’t any questionable smells or sticky spots, and they played decent music. Dean always felt tension from his shoulders melt away when he stepped through the door. Well, usually. He didn’t feel that tonight, but that had nothing to do with the bar. 

Dean and Benny were each two beers and two shots of whiskey in shortly after arriving. It was the whiskey that helped Dean tell his friend about why he’d been so distracted lately. To be fair, Benny’s reaction was acceptance after a bit of ribbing, thinking that Dean was pulling his leg. “I mean, if that’s gonna make you happy, brother, I’m behind ya. They better just treat you right.” 

Dean shrugged. “I guess there’s less of a chance of getting a douchy person with all of the steps she requires.” He couldn’t imagine someone being disqualified for having minor charges when they were young, but Pam wouldn’t require background checks if she was going to let anyone use her services. He wondered what her criteria were. She never asked if he had any deal breakers when it came to criminal history. Maybe she had a no tolerance policy? 

Benny’s question drew him out of his thoughts. “How do you plan a wedding with someone you never met?”

“Oh. Pam said she has a wedding planner. She asks us both our opinions on the usual things. Flowers, and food, and such. Then she mashes them together in a way that works, I guess. But I get to pick my tux, and I have to buy my own ring.” 

“What about your honeymoon?”

Dean shrugged. “I mean, I can put up a chunk of money right away and she’ll use that to book a surprise honeymoon  _ if  _ the person she matches me with does the same. I don’t have it, though. Not all at once on top of her fee.” At least Pam’s fee covered everything other than the honeymoon, his tux, and his ring. Looking up, even in the dim bar light, he saw the cogs turning behind his friend’s eyes. “Benny, no. What if they can’t either?”   
  


Benny shrugged. “Then you get that money back, right?” Dean nodded. “Good. Then you’ll use it to go on a cheaper honeymoon or put it in savings or something. It’ll be the wedding gift.” Dean just sighed. He was too drunk to coherently argue with Benny and by the time he got to the garage tomorrow, it’d already be taken care of. That was just how he and Benny’s friendship worked, and to be fair, Dean would do the same if their situations were reversed.

They stayed for another hour, drinking water because they both had to drive home. Benny clapped him on the back as they left the bar, squeezing just for a second. Dean read the meaning loud and clear, giving his friend a little smile and a wave as he climbed into his Baby to drive home.

★★★★

“Dean.”

“Hey, doc.”   
  


He’d told Dean to call him “Crowley” when he’d called to set the appointment, though that didn’t really feel  _ right _ to Dean, and so he’d settled on “doc”. Crowley was short and had scruff on his face and an English accent. He wore a nice suit and shiny shoes, and Dean thought he was overdressed for this but who was he to criticize? He also seemed kind of gruff and to the point. Crowley didn’t seem as amused with “doc” as Dean was. 

“Yes.” It was said with a resigned sigh that made Dean smile on the inside. “Why are you here today?”

“Pam didn’t tell you?” He felt kind of silly admitting it out loud to anyone else other than her and Sam and now Benny. Dean guessed that could be a problem, though, and it probably wasn’t the best start to his...whatever this was. 

“I’d rather you tell me in your own words.”

Well shit. It was one thing to  _ know  _ why he was here, it was another to  _ say it out loud _ . Dean rubbed the back of his neck, not quite able to make eye contact with the doctor. “C’mon. You already know why I’m here…” Crowley didn’t even crack a smile when he raised an eyebrow at Dean, which made Dean cough a bit and shift in his spot on the sofa. He looked at his hands now, not able to bring himself to look up at all. “Um. Yeah. I signed up for her matchmaking service and even after her telling me that it means that I won’t meet who she pairs me with until we’re actually getting married, I’m still interested in going through with it.” The words spilled out without him even taking a breath, because if he stopped to breathe he didn’t think he’d be able to start talking again, and when they were out there, hanging in the universe, they felt heavier, if that was possible. He wiped his sweaty palms on his jeans and finally ventured to look up at Crowley.

“What made you want to do this, Dean, even after knowing the specifics of the type of matches Pamela does?”    
  
That made Dean chew on his lip for a second and pick at his nails, seemingly forever caked in motor grease. “Adventure?” he finally offered.   
  
“Are you asking me, or telling me?”    
  
Jeez this guy was a dick. He thought about telling him so, but figured that wouldn’t help his case at all. After another minute of silence, which was really just Dean arguing back and forth with himself about actually baring his soul to this stranger, and the pros and cons of it, he actually spoke, because maybe he could salvage this and convince the doctor that he wasn’t a crazy nut and that he was emotionally mature enough to go through with this. He  _ wanted  _ it, and the depths with which he wanted it surprised even him. 

“Look. It’s weird. Most people would turn tail and run because arranged marriages are… Crazy, I guess. To a lot of people, especially when it’s a stranger doing the arranging. I get it. And yeah, at first, this was a drunken and lonely whim. So maybe I didn’t have the best thought process going into it, but it’s gotta say somethin’ that I’ve sat on this for almost two weeks now and am still here.”   
  
“It does,” Crowley agreed, making his notes. Dean hated note taking now. Not that he was all that fond of it before. “It doesn’t answer my original question, however, and I’d very much appreciate an answer.”    
  
Did Dean mention how much of a  _ dick _ this guy was?    
  
“I want… Someone to come home to. A partner, someone who I can share my day with and be someone they can share their day with. I want someone to go on adventures with me, help hold me up when I feel like sitting down. I want to be the one someone looks for that type of support from.”   
  
Dean saw the doctor nod and keep writing. “Why this route? Most people who want those things go down a more traditional road.”   
  
“You think I didn’t?” He realized as soon as he said the words how much of a douche he sounded like. Reaching to rub the back of his neck again, Dean apologized. “I did all that. Bars. Apps. Blind dates. Supermarkets. Facebook. Double blind dates. And when those didn’t lead to anything…” He shrugged. What more could be said about it?   
  
There was the shuffling of papers as Crowley looked through the notes that, Dean assumed, Pam had sent to him. “Your last  _ actual _ relationship was fifteen years ago, though.”   
  
“Yeah. I met Lisa through all the usual. Doesn’t mean I didn’t do them after her. Sam and Benny wouldn’t let me say no after so many times.” 

“What do you think will be the most difficult for you if Pamela were to find you a match, Dean?”

“Being in a relationship without an escape hatch,” were the first words to blurt out of his mouth without his permission. Shit. He hadn’t meant to open up  _ that _ much. And definitely not with something like that. Would that disqualify him? Would he be told he was too fucked up because of that to do this and that he should get himself into counseling instead?

Crowley speaking broke into his panicked thoughts. “Can you expand on that?”

★★★★

Dean walked out of the office feeling emotionally drained and tired and doubting himself. Were his answers the right answers? Crowley didn’t seem to like him. What was his report to Pam gonna say? Dean felt himself begin to shore up the walls around his heart, sure that Crowley would recommend to Pam that she not work with him anymore. His hand went to his phone before it stopped mid reach. He couldn’t call Sam or Benny. They’d want details. How could he tell them all of the stuff he’d told Crowley and expect them to still love him? Respect him? Dean shook his head to himself and got into his car to pull away from the tall, unassuming (and, in Dean’s opinion, misleading) building.

The next two weeks passed. This seemed to be a theme. Why was it only a week, then, after Pam matched you that you got married? Why not two weeks? Dean thought two weeks was reasonable… He shook his head. It was a circular thought pattern that he’d often found himself getting caught in. It didn’t do him any good, especially at home at night when he stared at his phone, willing it to light up. He just wanted to know the answer, even if it was that Pam and Crowley didn’t think she should match him. It was the being in limbo that was driving him crazy. 

He was lost in thought, beer now warm in his hand and the house completely dark because he hadn’t realized how late it was and didn’t turn the lights on. Dean jumped out of his skin when his phone dinged. After taking a few calming breaths, he picked it up to read the text message.

_ Hi Dean. I’ve found a match for you. _


	3. The Parents

**Summary for the Chapter:**

> Where Dean tells Bobby and Ellen.

Dean stared at the text. That was it? _I’ve found a match for you._ No other instructions. No next step. Nothing telling him what to expect or… Or anything! What was he supposed to do? Did he call Pam? Was Pam going to call him? Was he supposed to reply to the text? Why the hell was he acting like a teenage girl going to prom?

_Get it together, Winchester._

He texted out a reply to Pam asking what the next steps were. Her reply was quick to let him know that her wedding planner would be in touch with him in the next day or so and congratulating him. He stared at the last word, _“Congrats!”_ as his heart pounded in his ears. Dean dialed Sam’s number.

“Hey, Dean.”

“How am I supposed to tell them?” Okay, so he was panicking.

“What? Tell who what?” 

“Bobby and Ellen!” Who else would he tell? No one else mattered. Well, that wasn’t entirely true. There was Jo and Ash, but other than Sam and Benny there wasn’t anyone else he wanted to tell. 

“Dean!”  
  
“What?” Had Sam been talking? He couldn’t hear anything other than his own very loud thoughts. 

“What do you need to tell Bobby and Ellen?” Sam was speaking slowly. That meant that he was definitely talking and Dean hadn’t been listening to him. Shit. “Are you okay? Do you need me to come out there?” Sam had moved to Kansas City after he graduated law school so he could be closer to Dean and Bobby and Ellen. It was only a forty-minute drive at this time of night… Dean chewed his bottom lip, seriously considering it. It was Friday. Sam was off tomorrow…  
  
“Yeah. I got the text, Sam. She found me a match.” 

There was a beat of silence, which was enough to make Dean nervous. And then, “Dean! That’s great! I’ll pack a bag and be there in about an hour, okay? We’ll figure it out.”   
  
“Thanks, Sammy.” Just the knowledge that his baby brother was going to come over calmed Dean. He hadn’t realized that he was practically vibrating, both inside and out, until it started to calm. He breathed out a sigh of relief. “Stop for beer, okay?” Sam snorted.  
  
“Yeah. Okay, Dean. I’ll see you soon.”

When Sam hung up, Dean pulled himself out of his chair after a few more minutes. He had to keep busy or else he’d go crazy. Dean cleaned up the little bit of a mess that was in the living room, put some dishes into the dishwasher and wiped down counters. It didn’t take him nearly as long as he’d hoped, though. Mostly because he wasn’t ever home enough to make a mess. Food! Sam liked food.

Dean dug out some things to start to throw a meal together. He chose something that required a lot of chopping and slicing and whisking and stirring… Anything to keep his mind occupied.  
  
It didn’t work. 

Dean drew up images of who Pam had picked for him. Dark hair, because he’d specified that he was a brunette type of guy. Guy or girl? He supposed that there was more of a chance of a straight or bi chick than a bi or gay dude, right? No, that was silly. He’d had one night stands with as many guys as he’d had chicks. That made it more difficult to picture.  
  
Dean began his stirring, setting a timer. A chick. Something just told him that it was a chick. With long dark hair and warm brown eyes and a great smile. She’d come just up to his chest, and she’d have olive toned skin… Dean stopped and cursed, realizing he’d just described _Lisa_ of all people. “Get it to-fucking-gether, Winchester,” he repeated to himself under his breath. “Besides, you don’t _know_ it’s a chick. And it definitely won’t be Lisa if it’s a chick.” Great. Now he was talking to himself. 

Okay. Forget about looks. He continued his stirring. 

She’d be kind and understanding. She’d want to take Baby out to a field and stargaze on clear nights. But she wouldn’t want to drive, and she’d understand that when he refused to let her drive Baby, it didn’t mean he didn’t trust her. She’d like burgers and beer and pizza and all other kinds of greasy food, and not worry about eating them in front of him. 

She’d be strong and independent, the type of woman to scoff at him opening doors for her, but (not so) secretly smile when he did it anyway. She wouldn’t take his shit and she’d call him out on it when he needed to be called out. She’d have her own career that she was driven in and that she loved. She’d have her own interests and hobbies, too. Maybe she’d belong to a knitting group, or a women’s league tackle football team. She’d go out with her own friends without him sometimes, and she wouldn’t get bent out of shape when he went out for drinks with Benny after the shop closed for the night. 

_What if it’s a dude?_

The thought popped into his head just as the timer went off. He pulled the pan off of the heat and thought about that for a bit. The laundry list of qualities he listed wasn’t strictly something he liked in girls. They were things he looked for in a partner, regardless of gender. He supposed a dude could be and like those things. At least some of them. A dude definitely wouldn’t be part of a women’s league tackle football team. He’d like to cuddle just as much as he liked sex. Maybe he’d like to bake? Dean would totally love that, especially if he liked to bake pies...

It was a long list, probably impossible to find all in one person. Dean knew that in dreaming up this dream girl, he was setting himself up for some sort of disappointment and he didn’t want to think about that.  
  
Dean put the last ingredients into the pan of food and set the whole thing in the oven, setting the timer again. 

Would whoever Pam chose want to live here? Or would they want to live at their place? Or maybe they wanted to buy something completely new? Dean didn’t want to give up his house. What if he chewed with his mouth open? Or was a vegan? Dean didn’t think he could be with a vegan…  
  
“Dean?” 

He was pulled out of his thoughts by his brother’s voice and Dean was grateful. “In the kitchen, Sammy.” Sam came in and set his overnight bag on the floor and the beer on the counter before pulling Dean into a tight hug. “Can’t breathe, Sammy…”

“Sorry.” He stepped back but was still grinning stupidly at him. Dean rolled his eyes and moved to put the beer in the fridge, pulling out two cold bottles and handing one to his brother. “You don’t seem excited?”  
  
Dean shrugged and took a mouthful of his beer to give him a second to form an answer. “I am. It’s weird, though. To think that I’ll be married by next week, you know? And having no clue who it’ll be to… What if it doesn’t work? If we hate each other?” 

“Then you go your separate ways.” Dean picked at the label on his beer a bit, struggling with whether or not he believed in divorce for himself. Sam, as always, seemed to see the words he was thinking in a bubble over his head. “Dean, you did think about this possibility before now, right?” Dean shrugged and Sam sighed, rubbing his hand over his face. 

“It didn’t seem real, Sam! I didn’t think I’d get through the psych portion! Or that she’d find a match for me, or that she’d even _want_ to find one for me considering my history with people. Even this conversation just proves how fucking damaged I am, man.” 

“You’re not _damaged_ , De. You had some bad luck, and then other priorities. You’re not the only person who was hurt, and then spent the last ten years building their own business, and the last five years saving to buy his own house.”

“I guess.” 

The timer dinged and Dean set his beer down to pull the food out while Sam moved to pull plates and forks out for them. It didn’t take too long before they were sitting at the table, digging into the food Dean had made them. “So how do I tell Bobby and Elle?” Dean asked after they had full plates.

Sam thought for a minute, chewing on a piece of chicken. “Over dinner? I mean. They’re gonna be shocked for sure, but I think they’ll support you.”

That was the issue, really. He _thought_ that his pseudo-parents would support him but this was so out there. It wasn’t like coming out to them, when he knew that they’d support him. This was off-the-wall-out-there. “What if they don’t?” he finally asked Sam.

“When haven’t they?” Fair point. But it didn’t make him less nervous. “They already know I’m in for the weekend and we’re having dinner with them tomorrow.” Dean’s head shot up as he glared at Sam. “If I didn’t call them you would’ve put off telling them until the day before and _then_ they would’ve been pissed at you.” Sam was right, but Dean wasn’t about to tell him that.

★★★★

Bobby was an old friend of their dad’s. Well, “friend” was a bit strong, but it worked out to the same thing: that Bobby was the only one to step up when Dean and Sam needed a home. Dean had never been able to express his gratitude to the gruff man, and he probably never would. 

The house hadn't changed at all since they were kids and just walking up the rickety old front porch steps brought Dean a sense of comfort. It was two stories. It had peeling paint and the porch looked like it was about to cave in. There was a layer of dust covering everything from the scrapyard the house sat in the middle of, which served as Sam’s and Dean’s playground growing up. It was and always would be home.

“Hey, Bobby.” Dean hugged the man who raised them when the door opened before stepping into the house to let Sam say his hello. “Is Elle in the kitchen?”

“Where else is she ever when you boys come over?” True. Dean smiled at him and made his way into the kitchen to greet Ellen. 

Bobby had met and married Ellen when Dean was twelve, about two years after he and Sam had come to stay with him. She had her own daughter, Jo, and she folded Dean and Sam into her mothering ways seamlessly. Dean hugged her from behind. “Hey, Elle. Need some help?”

The four of them were sitting down to dinner twenty minutes later. Dean focused on Sam, keeping the spotlight off of him. Sam gave him looks, nudged his foot underneath the table, but he ignored him. It just… He wasn’t ready. Sam let him get through all of dinner, and then Dean jumped up to help Ellen with the pie he knew was in the kitchen. There was always pie in the kitchen when he was visiting because she was just awesome like that. Dean saw both Ellen and Bobby raise their eyebrows at his jumping to help clear the table and reset it for dessert, but he ignored them just like he was ignoring Sam. If he ignored it, then he magically wouldn’t have to say anything to anyone.

Except he wasn’t that lucky and less than five minutes later everyone was sitting around the table again with pie and ice cream and whipped cream and coffee and anything else that he could think of that they might need. “Why are you so twitchy, boy?” Sam smirked at him, and Dean muttered an insult at his brother.

Dean rubbed the back of his neck and then around to the front, rubbing his hand over his face. “I, um. I need to tell you and Elle something and I need you to not freak out right away.”  
  
“Are you in trouble, Dean?” Ellen looked worried, and she gave a side glance to Bobby. “Is the garage okay? The house?”

He shook his head. “No, no. Nothing like that. Everything is fine. It’s just that, um.” After pausing for another minute, he figured there wasn’t any other way than to dive in head first. “I’m getting married. In a week.” There was stunned silence, but Dean could see Sam smirking from the corner of his eye.  
  
“You knew about this?” Bobby accused, looking at Sam. “You’re seein’ someone?” That was to Dean.

“Not… Not exactly.”

“Boy, you’d better start makin’ some sense here.”

So he started from the beginning, going over everything from the drunken night, to meeting Pam, and then Crowley and finally the text. The silence that followed nearly killed Dean. 

Ellen spoke first. “This is what you want? What happens if it doesn’t work out? Your business? Your house?”

“Sammy’ll draw up a prenup for me. What we come in with, we go out with. And anything we get while married, outside of the profits from the garage, we split down the middle.” Dean smiled at the two people who raised him and Sam, the only two people who had ever shown him unconditional love and respect as a parental figure. “I’m… I want this. I’m _ready_ for this.”

“I just need to know one thing.” Dean looked to Bobby who’d been silent so far. “Do I gotta wear a tux?” Dean barked out a laugh.

“Nah. Wear whatever you want, Bobby.” He meant it, too. If his spouse-to-be got upset at his pseudo father wearing jeans and a flannel, then it wasn’t meant to be anyway.


	4. The Wedding Planner

**Summary for the Chapter:**

> Where Dean picks flowers, colors, food, and music.

“Hi Dean, my name is Tessa. I’m one of the wedding planners who works with Pam.”

Tessa was pretty. She had brown hair that came to her shoulders and big doe eyes. Dean could admit that he was attracted to her, and would probably hit on her if he met her in a bar. “Hi.” Okay, he was nervous again. That seemed to be his running theme throughout this entire process if he was honest. Tessa seemed to pick up on it, though, and she smiled at him.

“It’s my job to help you and your match not only pick out and put together your perfect wedding, but to make sure it’s executed flawlessly. I’ll be with you today, and then I’ll be in touch with you throughout the rest of the week. I’ll also be on-sight on your wedding day for the entire day, okay?” 

That was something Dean hadn’t expected, if he was honest. This whole thing seemed to be one and done with a lot of the people he was working with through Pam. It worked to put Dean a little more at ease with the process.

“Do you have anyone you’re sharing this process with? Best man? Best girl? Parents?” 

Dean hadn’t really thought about that. He chewed on his bottom lip as he thought. “Well my brother is my best man. He works in Kansas City, though. He’ll probably come to pick out the suits and then the bachelor party but not the other stuff. My parents…” Dean shook his head. No reason to get into that. “Bobby and Ellen raised me. They’ll probably be involved a bit but, uh, I didn’t think to invite them to this meeting.”   
  
Tessa nodded. “Well if you’d like to call them now, we can focus on some of the smaller aspects until they get here?” 

Dean’s eyes lit up. Ellen would be heartbroken to know she didn’t get to be a part of this process… He pulled his phone from his pocket and dialed her number. The conversation was fairly short, but he knew it meant a lot to her. “Bobby’s working but Ellen will be here in about thirty minutes?” Tessa smiled and nodded again.

“How about some coffee while I pull out some samples?” she suggested. “I have photographs of some ring ideas for your new spouse, nothing very personalized of course, but just so you have an idea when you go to the jeweler. That appointment is Wednesday, by the way, and the tailor appointment is Thursday.”    
  
“Yeah, okay.” He used the Keurig machine to make it easier and faster, returning to the table a few minutes later with two cups of coffee, some cream and some sugar. Dean preferred his black, but he didn’t know how Tessa took her coffee. She slid some photos in front of him while taking the cup.

There were three options for a dude and for a chick, but they were all similar options. One looked like brushed silver metal but was otherwise plain, one was a matte black metal that looked pretty badass, and the last was a gold band that looked to be hammered. Dean read over the descriptions. He discarded the silver looking one (it was platinum and way out of Dean’s price range) and then studied the other two. Neither were traditional, really. Well, none of them really were, he supposed. “Do I have to pick one now?” he asked.   
  
“No. The jeweler will have the ring sizes of you and your spouse. You’ll go and pick out the ring you want, it doesn’t have to be these, and they’ll both be sized and delivered to you on Saturday before the ceremony.”    
  
“Okay.” He set the pictures aside then, since he wasn’t going to pick anything out today. 

“What about the menu, Dean? Are there any special diets? Vegetarian? Vegan? Diabetic?” Dean thought for a minute and shook his head.

“My family is mostly omnivore. Sam likes healthy stuff, though, so maybe a healthy option that isn’t just a salad?” Tessa made notes, nodding.    
  
“Baked fish, maybe?” Dean thought and then shook his head. She chuckled and scratched out what she’d just written. “Okay. Baked chicken with roasted vegetables and rice?” That sounded more like Sam and Dean nodded his approval. “Great. And now… Let’s look at the venue?” Tessa suggested, pulling up some images on a tablet. “We need your opinion on a venue for the ceremony and for the reception.”    
  
Dean heard the front door open and close, and he breathed out a sigh of relief which was to Tessa’s amusement. He stood to hug Ellen, giving her an extra squeeze because he didn’t know what he would have done if Tessa hadn’t suggested inviting her to take part. He made introductions and poured Ellen a cup of coffee while she started to swipe through the photos.

“Now the fees you paid to Pam are combined with your Match’s. There’s a limit of ten per side. It’s small, but anything larger would make Pam’s fee exorbitant. So the venues are very small. Each venue has a catering hall and a ceremony spot,” Tessa explained. “Wherever your ceremony is, that’s where your reception will be.”   
  
“Then why are we choosing between six photos?” Ellen asked, flipping back and forth between two a few times before moving on.

“Well it’s a compromise. I would like Dean to rate each venue one through three, with an emphasis on which is more important to him: ceremony space or reception space. His Match will do the same and I will do my best to find a compromise for both.”

“What if they like two entirely different spaces?” Dean thought it was a fair question when he came to sit next to Ellen.

“Then I’ll come back with the originally high rated one gone and ask Dean to pick between the two left, the same for his Match. If there really can be no compromise, then I’ll consult Pam.”

Dean could tell that Tessa hated that particular option. “It’s just…” Dean shrugged. “What’s the big deal, Elle? So I’m not super crazy about the place. We’ll have our own reception a little later, once we’re sure it’s gonna work. At a place that we both love.”

“That’s not the point, Dean! Your wedding photos will be in this space. You should feel comfortable and at ease there.”   
  
He chuckled. “Elle. It’s going to be my wedding day. To a person I’ve never met before in my entire life. There is not one place on this Earth where I would be comfortable and at ease on that day.” Ellen huffed, signifying to Dean that he’d won that particular battle. They flipped through the pictures, and Dean gave Tessa his rankings with input from Ellen. 

“Great.” She marked down his choices. “Now. Flowers.”   
  
Dean groaned. “Please, Elle. Tessa. What do I know about flowers?”

“Just pick the ones you like best, honey,” Ellen told him, flipping through the three photos of the options. Luckily, they were labeled: Roses, Peonies, and Tulips.

_ Not roses… _ They were overdone. Then again, so were tulips. Weren’t they? Were roses, even? Dean chewed his bottom lip, clearly unsure.

“There’s no right answer, Dean. It’s just what you want,” Ellen assured him, rubbing his back for a second. He nodded, but he still felt like no matter what he chose, it’d be wrong.

Well. If he was going to be wrong no matter what… “The peonies, then.” 

“Great!” Tessa marked that down, and took the tablet. “We’ve chosen the food… So all that’s left is music and colors.”   
  
“Now we’re talkin’!” Dean’s eyes were wide and bright, showing his excitement over talking about a subject he was passionate about. “Lynyrd Skynyrd, All Time Greatest Hits. CCR, Chronicle Volume One. Oh, Zeppelin, of course. Metallica. The Stones, obviously. AC/DC. Oh! And -”   
  


“Um, I think I have an idea of your tastes, Dean,” Tessa teased with a little smile. “What about a wedding song? Something to dance with your Match to?”

That stumped Dean. He didn’t know who he’d be dancing with. He didn’t know what taste in music they had. What if they wanted a boy band song and that was what played? Or rap? Not that he had anything against other types of music, per se, they were simply inferior to the great rock hits he loved. “How’s this gonna work? I mean, what if our tastes in music are opposite?”

“Well, you’ll have your dance with your Match, and then the… Parent’s dance. You with Ellen, and then your Match with his or her mother or father. So between me and Pam, we’ll choose one of your songs for your dance, and one for the parent’s dance.”

That made sense. Dean sat back, going through his extensive music collection in his head, but still coming up blank.

“What about  _ When I see You Smile _ ?” 

It hit instantly and Dean beamed. “Yes! Perfect.” 

“Great! The last thing we need to choose is colors. What do you think, Dean?”

“Black?” He caught the movement from the corner of his eye a split second before Ellen’s hand cuffed him upside his head. 

“No.” Dean rubbed the back of his head where Ellen had whacked him. 

“But Elle - “

“Dean, no.” Ellen took the tablet to scroll through some digital swatches that Tessa had. “There.” She pointed to a sage green color. “And maybe a grey as the neutral.” She looked to Dean for confirmation but he just shrugged. He didn’t really care about the colors much, and he trusted Ellen to choose ones that would look good.

“And the very last thing is the honeymoon. Your three choices are Hawaii, Yellowstone, and Disneyworld. Pam tries to offer three completely different experiences to try and find something that everyone will like.”

“Um. Disney, I think.” Hawaii required a plane. They could drive to Florida, make it part of the trip. “But Yellowstone would be my second choice.”

Tessa took her notes and tucked her tablet away. “You’ll need to get me your guest list by the end of the day, if possible. I know it’s a tight timeline but, well, so is the entire thing. You won’t be able to mail the invitations, but I will get them to you so you can hand deliver them to your friends and family.” Dean nodded. “And, let’s see. Today’s Monday…” She tapped a few things out on her phone. “Your appointment with the jeweler is Wednesday and…” A few more taps. “The tailor on Thursday. You won’t have anything planned then until Saturday at one when you’re expected to be getting married!” She sounded a little too cheery in Dean’s opinion, but he just nodded anyway, committing the days to memory.

She left soon after and Dean let out a long huff of a breath, finally relaxing a little bit. Ellen patted his hand. “When’s Sam coming home, sweetie?”

“Thursday around lunch, I guess. He told me to let him know when I was going to the tailor. I’ll let Bobby know too. We can go together.” 

Ellen smiled. “He’ll bitch and moan, but he’ll like that.” Dean laughed and nodded, hearing Bobby in his head already. 

“He doesn’t have to wear a suit. I just thought he’d like to go with us.” 

“I know, sweetie. So does he.”

Ellen left soon after and Dean cleaned up the few cups that they’d used and sat down to start a list of people he wanted to invite. Sam, Bobby, Ellen, Jo, Ash, and Benny took six of his ten. That was where his brain stopped, though. He sat at his dining room table, scrolling through his cell contacts. Dean made a list of possibilities, but scratched them off one by one as he went through them again. One name stuck out, and Dean stared at  _ Garth _ for a while. 

He’d known Garth for years. They went to high school together and… Well, you try to  _ not _ be friends with him. They hadn’t spoken for a few months, but that was the way their friendship went. A few months of no contact and then he’d join him and Benny for a drink for a few weeks, and then be off doing his own thing again, or Dean would.

After another few minutes of indecision, Dean went back to his contacts and tapped Garth’s name to call him.

An hour later, Dean had two more names added to his list. Two more spots. Nothing said he  _ had _ to invite ten people. He could invite less… But he didn’t want his Match to think that he didn’t have friends. He didn’t want to look pathetic.

He gave another scroll through his contacts with a huff. After a second pass through, Dean’s finger hovered over Jody’s name. She had been the one who dropped him and Sam off at Bobby’s house, and had stayed in touch over the years. She was someone he felt comfortable talking to about some serious stuff when he didn’t want to worry Bobby. 

Before he could chicken out, Dean tapped her name to call her. This call took longer, and resembled the conversation he’d had with Bobby and Ellen two nights ago. Except Jody had a lot more questions. Damn cop mentality. Dean felt like he’d spent the entire last two weeks answering questions. 

“Jods,” Dean interrupted, shaking his head a little in exasperation, glad that she couldn’t see it. “I appreciate your worry but Pam already did our background checks.”

“Yeah, but who did she use, Dean? Someone reputable? There are a lot of companies out there that will tell you what you want to hear, or they aren’t very thorough, or -”

“Jody. She has a sterling reputation. Her Matches have never killed each other. I promise.” He heard a huff and smiled a bit. “So I’ll see you and Donna on Saturday, right?”   
  
“What? Of course we’ll be there!” 

“Good. Bye Jody.”

Dean didn’t give himself time to second guess his list. He sent it to Tessa immediately, locking in his choices. Taking a deep breath, Dean let it out slowly and stood up, going to his fridge for a beer.


	5. The Jeweler

**Summary for the Chapter:**

> Where Dean picks his spouse’s wedding band.

Dean had taken all of Monday off to meet with Tessa. In reality, she was gone by one and Dean had sent his list of guests to her by two. By three he was nearly climbing out of his skin and went to the garage to keep his brain occupied until Benny literally kicked him out near eight.

He didn’t sleep a wink, and was back to the shop by six. Benny rolled his eyes at him as he walked through the door at eight. “This what I got to look forward to the rest of the week, cher?” he asked. Dean only shrugged in response, focusing on the engine in front of him. He’d accepted a custom re-build job months ago and parts had come in over the weekend. It was the perfect project to keep his mind busy. “This ain’t healthy, Dean.”

“Yeah I know it. But it’s just ‘til Saturday, right? And Sammy’ll prolly keep me outta here all day Friday, too.” He gave his wrench one last good pull before being satisfied. “And I wanna get this job out before then.” It was almost done, he could probably have it finished by the end of today if he kept his head down and worked through the day.

Dean saw Benny shake his head but his friend didn’t say anything else and got to work himself. He was grateful for it, even though he felt guilty about being grateful for it. Benny was trying to be a friend, but this was uncharted waters and Dean felt like he just needed to deal with the next few days however his brain told him that he needed to. He definitely appreciated that Benny seemed to get that. 

It was busy. He didn’t get to keep working on the re-build, as emergency tows came in and he had to put on his Boss!hat to make decisions about priorities, handle unhappy customers, and sign for a few orders. It was nearing noon when Dean’s phone rang, flashing Tessa’s name. His brow furrowed as he answered.

“Hi, Dean. Listen. Your Match is at the jeweler, and has a request.”

“Okay?” It was odd, he was sure, that this type of communication was happening at all he was sure.

“They’re finding it...difficult to choose a ring for someone they don’t know and are wondering if you’d agree to pick out your own ring and leave an inscription for theirs?” Oh. That wasn’t what Dean had been expecting, but it made his job a hell of a lot easier since he didn’t know the gender of his Match. He was pretty sure he’d pick out different rings depending on that.

“Do they know I’m a dude?” he asked rather than answering the question. There was a long pause from Tessa, and Dean realized that she probably couldn’t tell him. “No, it’s okay. I shouldn’t have asked, sorry. That’s fine, Tessa. Whatever they want is what I’ll do. It’s easier for me, you know?” He could hear her breath of relief.

“Thanks, Dean. I don’t think it’d make much of a difference, but… Rules.”    
  
“Yeah, I get it.” 

They said their goodbyes and hung up, leaving Dean with something new to obsess over as he worked. What sort of inscription could he offer? He wasn’t great with words at the best of times, and here he was, expected to put together something meaningful that would, theoretically, sit on the finger of his husband or wife for all of time. It was a ton of pressure that he wasn’t really ready for. At least if he’d chosen a ring and they didn’t like it, the two of them could go and buy a new one together. 

Dean thought about texting Sam, or asking Benny or Ellen for help but this seemed too personal. It seemed like it was something he needed to do on his own. He was back on the floor now, working on a car that had come in during lunch, making lists of options in his head. He could go cheesy, find something on the internet that was “classic” and “timeless”, but that seemed...impersonal. Dean thought about a Vonnegut quote, but he didn’t really lend toward romance or wistful quotes. There was Hemingway, but the few that came to mind weren’t quite right for their situation. 

As he closed the hood of this particular car, Dean turned his brain toward the other thing he knew everything about: movies. There were endless options, he knew, but the ones he used most often weren’t appropriate. Maybe he’d spend the night not underneath the hood of a car, but up to his eyeballs in chick flicks to try and find the right thing to inscribe on his Match’s ring. That lead to the question of which movies should he watch? He had a few at home, stashed away and hidden so that Sam wouldn’t find them.  _ You’ve Got Mail _ ,  _ Dirty Dancing _ , and  _ The Notebook _ were some of his very favorites. He could start with those. One of them had to have  _ something _ he could use.

As he continued to think about it, Dean realized that he knew those movies inside and out, and nothing was right for the inscription. That meant renting movies and hoping to stumble across something. That didn’t sit well with Dean, but since he wasn’t willing to ask anyone for recommendations and face ridicule, it was the best he could think of. 

He didn’t worry about it for the rest of the day. Instead, he focused on the cars and the customers and before Dean knew it, they were closing the shop for the night. “You actually goin’ home, brotha?” Benny gave him a disbelieving look, which Dean shrugged at. 

“The planner called and asked me to pick my own ring but leave an inscription for the other person’s, so I got homework I guess.” 

“Got any ideas?” 

They walked out of the shop together, Dean setting the alarm and locking the door. “A few. It’s a lot of pressure. It’s not like we love each other and have inside jokes and stuff, you know?”

“Find somethin’ that can be your first inside joke together.” Huh. Dean hadn’t thought about it like that and he nodded to the suggestion. Hopefully something would catch his attention that was like that.

Dean said goodbye to Benny and climbed into Baby to head home. 

He spent the night watching four different movies. By the third one his eyes were watering and he was exhausted, but he still hadn’t found the perfect inscription. Maybe there wasn’t such a thing. Sighing, Dean talked himself into one more movie. He wasn’t going into the shop tomorrow morning and his appointment at the jeweler wasn’t until ten, so he could sleep in a little bit. He got up to make himself a cup of coffee to help him stay awake for the entire thing and returned to the sofa, clicking start on the last movie of the night.

He struggled to get through the movie, if he was honest, and it probably wouldn’t ever be something he pulled out to watch again, but it gave him his inscription. It wasn’t something that was said in any big romantic statement in the movie, but it captured his own personality (in his own humble opinion). Dean went to bed with a huge weight off of his shoulders, and he even slept pretty peacefully for the first time since he’d received the invitation to meet with Pam.

Dean was early to his appointment. He couldn’t help it. His nerves had started to pick up again around eight and he didn’t make it past nine before leaving the house for the thirty minute drive to the jeweler that Tessa had sent him the address to. He wondered why it was so far from his house, but figured maybe it was close to his Match’s house? It could be that it was just a random jeweler that Pam had worked with. Dean wasted some time getting a cup of coffee, which was probably a bad idea considering how jittery he already was. But it was coffee or whiskey, and coffee was the more socially acceptable choice at nine thirty in the morning.

Finally, at ten to ten Dean stepped into Jewelry by Balthazar. It was small. Tiny, even. There was one long case that ran most of the length of the customer area, and one half that size sitting perpendicular to the first. The smaller one was where he saw the rings and wedding bands, and so he moved over to that one to look. 

A blond man came out from the back and greeted him in a cheery English accent. His shirt had two too many buttons open showing more chest than Dean would have thought acceptable in a business setting, but when he introduced himself as Balthazar, it made more sense. 

“What are you looking for?” Well wasn’t that a loaded question?

“I need two rings,” Dean started. “One silicone, a little on the thinner side. I’m a mechanic and I want to stack the regular ring on top of the silicone one.” Balthazar nodded, but he didn’t take notes like the other people Dean had met through Pam. 

“And for your band? Gold? Platinum?”

“I don’t think I paid Pam enough to cover platinum,” Dean retorted, looking at the rings in the case instead of at the jeweler who was chuckling.

“True, darling. You’d pay the difference out of pocket. But a mechanic?” Dean looked at Balthazar and nodded. “Stay here.” There was no more explanation before the jeweler disappeared into the back room behind the counter. Dean could see various machines that all looked foreign to him. While he waited, Dean looked through the case again, but nothing really caught his eye. They were all classic, he supposed. Not really him. He looked up with interest when Balthazar came back out holding a ring box. “A customer custom ordered this beauty,” he told Dean, opening the box.

Inside sat a silver colored ring, but inlaid in the middle of two thin silver strips was beautiful gear work.

“It’s tungsten carbide,” Balthazar offered, “and it can be sized for you.” 

It was...perfect, really. Dean couldn’t believe how quickly Bathazar had read him. 

“It’s a tad more expensive than your fee to Pam…” Balthazar gave him a number that nearly made him choke. “But I kept the deposit from the original buyer so I’ll charge only half it and waive your engraving fee. There aren’t many people who would be interested in a piece like this, and I’d like to sell it rather than melt it down.”

Dean did mental math. It wasn’t an expense he’d counted on but the ring was perfect. Even he could see that. Chewing his bottom lip, Dean nodded after another minute of back and forth with himself. “Yes, I’ll take it.” 

“Wonderful!” Balthazar snapped the box shut and handed over a form. “Put your inscription on this, and I’ll get your bill.”

Picking up a pen, Dean filled the form out and slid it back across the counter. When Balthazar came back with his bill, he handed over his rarely used credit card to pay the bill. “Can I take a picture of the ring? For my brother?”   
  
“Of course, darling.” Balthazar took the card to process the payment and came back with both the card and the ring. Dean snapped a picture, sent it to Sam, and signed the receipt.

“Left hand please, Dean.” Balthazar was holding a large key ring with tons of little rings attached. “I just need to size you so there’s a perfect fit.” Oh. Dean held his hand out and let the jeweler do his thing and make the only note Dean had seen him make for the entire appointment.

“How will I… These…?”   
  
“Oh, yes. They will be messengered over to the lovely Tessa who will hand them off to your respective…” He paused for a moment, clearly looking for the right word. “Seconds.” 

Dean couldn’t help but be a little bit disappointed in the fact that Balthazar didn’t slip up and give him  _ something _ about his Match. He smiled and thanked Balthazar, leaving the shop just as his phone rang. “Heya Sammy.”   
  
“Dude. How’d you find that ring?”

★★★★

Dean’s phone rang later that night, flashing Tessa’s name. “Dean. I heard you found your ring! I’m so excited for you!”   
  


“Yeah. It was fate, or something. Are you calling to let me know when my appointment with the tailor is?” 

“Yes, actually!” He heard paper rustling as he sat in his chair with a beer. “Tomorrow at noon okay?”

Dean nodded and answered, “Yeah, that’s great. My brother and Bobby are gonna be with me. Is that okay?”

“Yep!”

Tessa gave Dean the details and told him she’d also text them to him. Dean thanked her and hung up, texting Sam and Bobby the details.


	6. The Tailor

**Summary for the Chapter:**

> Where Dean picks his suit. To match the wedding theme (is that a thing?).

When Dean, Sam, and Bobby walked into the tailor shop the next day, they were greeted by a tall, thin man with a long, oval face and a large forehead. “Good morning. You must be Dean. I’m Julian, it’s lovely to meet you.” 

Julian was wearing a dark blue suit with a grey shirt. He wasn’t wearing a tie, but his shirt buttons weren’t open, either.    
  
“Uh, yeah. This is my brother Sam, and our surrogate father Bobby.”

The tailor shook each man’s hand. “Welcome to my shop. I’ve spoken with Tessa who asked me to let you know the theme of your wedding to help you better choose your suits.”

“Theme?” Dean asked, his head cocked to the side a bit as he tried to wrap his brain around that. “That’s a thing?”

  
Sam shook his head. “Of course it’s a thing, Dean. How do you think you get everything to match everything else?” Dean just shrugged. He’d never given it much thought, really.

Julian was smiling at them. “Your wedding theme is a vintage rustic, Nature-Meets-Machine.”

“Your match must be the ‘nature’ part,” his brother dead-panned, and Dean nodded his agreement, not really sure how that theme would help him pick a suit. 

Julian jumped in to help since Dean’s face was probably reading blind panic. “I’ve picked out three suits that I thought you might like based on what Tessa sent to me.” He gestured over to three mannequins. All three suits were similar in style and cut, but their colors weren’t what he’d have picked. One was a medium grey, and when Dean went up to it he could see miniscule pinstripes running down the material. The second was a dark moss green with no pinstripes or any other sort of pattern. The third was a dusky slate blue. The third suit didn’t have any pattern, either. 

Dean stared at the choices, not confident enough at all to make a choice. What if he picked something that clashed? “Can I know what my match picked?” he asked, feeling like he already knew the answer.

“Your match was given the same color choices, whether for suits or dresses,” Julian answered with a small smile. That wasn’t what he asked.

“So no?”

“What does it matter, Dean?” Sam asked gently. “The colors all look great together so..?”   
  
“Yeah but what if… What if they picked grey for their best man or woman or whatever, and green for themselves. And I choose grey for me and green for you? Then it looks like I’m marrying the person in grey and not the person in green.” 

Sam shook his head. 

“You shake your head now, Sammy, but you won’t be when you’re marrying her sixty year old Aunt Myrtle who is standing with him!”

“I’m not marrying  _ anyone _ , Dean.”

“But it’ll  _ look _ like you are.”

Bobby huffed. “Will you two idjits stop bickering? Why don’t Sam just call this wedding planner girl? Ain’t like he’s the one gettin’ hitched.”

Dean shrugged. “She won’t say anything.”

“You don’t know that.” Bobby reached for Dean’s phone to hand to Sam who unlocked it using his passcode easily. Dean didn’t bother wondering how Sam knew the passcode.

Sam put the call on speaker phone. “Hi Dean, how’s the tailor going?”

“Hi Tessa, this is Sam, Dean’s brother. We’re having a bit of trouble.”

“Oh?” She sounded genuinely concerned, like she wasn’t concerned  _ just _ because her job depended on happy people. “What’s going on?”

His younger brother described the problem, and Dean couldn’t help but bristle a little when Tessa chuckled. 

“Dean?”   
  
“Yeah?”   
  
“Choose the grey suit for Sam and have a glass of champagne. Relax. This is supposed to be an exciting thing.” 

Oh. That… He could feel the tension seeping out of his chest and back at the words. That made it easier; it made it better. “Thank you.” He could hear the sigh of relief in his own voice, and he could hear Tessa smiling over the phone.

“You’re welcome, Dean. I will see you the day after tomorrow.” Sam ended the call and handed his phone back to him. Dean gave him a sheepish ‘thanks’ while Bobby shook his head at them both and Julian waited patiently for Dean’s decision.

“Grey for Sam, please. And for Bobby.” Julian nodded and an assistant came out with three glasses of champagne. Dean couldn’t remember the last time he had champagne, but it seemed rude to refuse it so he took one of the flutes, followed by Sam and Bobby. 

Julian took Sam first to take his measurements and to try on suits. Julian paired the suit with a crisp, white shirt and a pair of sharp looking brown shoes. The pocket square and tie, he was told, would match whatever suit he chose. There were a few alterations that needed to be made and the tailor took down his notes. Bobby was next, his suit the exact same as Sam’s, except his tie and pocket square would match the suit that Dean  _ didn’t _ choose. As Dean finished his champagne and declined a second glass., he noticed Bobby’s glass was just as full as it had started out. 

“So Dean,” Julian asked after taking the rest of Bobby’s measurements. “Do you know which suit you’d like for yourself?” 

Dean felt like green was the obvious choice for him, and maybe he’d do something different. But would he look silly? Like he was trying too hard? He looked between the two for a long minute before telling Julian that he wanted to wear the green suit. The tailor took his measurements and then promised all three suits would be delivered to his house on Saturday morning. 

“Tessa wanted me to give you this itinerary for Saturday,” Julian told Dean, handing him an envelope. “It tells you when to expect the suits, when to be at the venue, and the like. If you have any questions, you of course can call her at any time.” Dean thanked him and tucked the envelope into his back pocket as the three of them left the shop. 

Sam clapped him on his shoulder as they came up to the car. “So. Let’s talk about your bachelor party…” 


	7. The Best Man

**Summary for the Chapter:**

> Where Dean attends his bachelor party

**Notes for the Chapter:**

> [Chaotic_Librarian](https://archiveofourown.org/users/Chaotic_Librarian) was an amazing help with this chapter, and I have no words that are adequate enough to express my thanks.

“For the last time, Sammy. No. Strippers.”

Sure. Sam was his best man and it was his job to plan and execute the bachelor party. And most would say that Dean should not complain and be grateful that his brother was doing this for him. But he was _engaged_. Kind of. Maybe. Was he? He was. Because if he didn’t take this part of it seriously then wasn’t that just disrespectful all together? Dean felt like it was.

“Okay. Fine. No strippers,” agreed Sam. “But drinking? Drinking’s okay, right?” 

“Drinking is definitely okay.” 

“You, me, and Benny?” 

“You’re the party planner, princess.” 

Sam stuck his tongue out at him. Dean laughed. He stopped laughing, though, when Sam spoke his next words. “Be ready to go by two. Bring nice clothes for tonight and something comfortable for tomorrow.”

“Wha-- Two? That’s…” He looked to the clock. “That’s in an hour, Sammy. How’re you gonna pull off planning an entire bachelor party in an hour?”

Sam shook his head. “You think I waited until _now_ to plan something?” he asked, watching Dean as he worked through that in his head. “De, it was planned the day after you told me Pam found you a match.”

“Oh,” was all that Dean could manage. 

“I have a whole itinerary planned.” Dean opened his mouth to ask a question, but Sam interrupted him. “No, you can’t see it.” Dean pouted a bit at that. “Let’s go. I’m already packed,” Sam gloated, falling onto the sofa and picking up the remote control.

“That’s because you had advanced notice!” Still, Dean got up and went to pack, wondering what Sam had planned.

It was close, but Dean was just on time with being packed. He stopped a bit short when he came into the living room with his overnight bag and saw a limo with black tinted windows and chromed rims sitting in front of his house. “Sammy, is that…”  
  
“A Charger limo? Yes it is. And Benny is already in it, so let’s go!” 

He was still a bit shell shocked, but he nodded and followed Sam out to the waiting limo. The driver took his bag from him and, he assumed, added it to the trunk with Sam’s and Benny’s. They were pulling away from the curb and Sam was thrusting a cold beer into his hand before he realized it. Sam lifted his bottle into the air and Benny followed suit. Dean felt a bit of heat in his cheeks but he did the same with his own beer. Nothing was said, and Dean appreciated that from his brother. They tapped the bottles together and drank.

“So how’s it feel, brother?” 

Dean took a minute to think about his response to Benny’s question. “Surreal. I mean, I get that a lot of that is probably the, uh, timeline of it all.” Benny snickered into his beer. “But yeah. Like, it feels like I was filling out that survey last night or something, you know?” 

“Honestly, I didn’t think you’d ever get married.” Dean shrugged to the comment.

“Wasn’t really on my radar. Not even that night. I was too drunk to realize what _‘a different kind of matchmaker’_ meant. And by the time she figured out I didn’t know, I figured I was in too far to back out.”

They chatted and laughed, the way the three of them always did when they got together. It was nice, and actually perfect which Dean shouldn’t be surprised about because it was Sam who had planned this entire thing. 

They were two beers in when the trip down memory lane started. It started pretty tame. First crush. First kiss. Sam blushing and Benny and Dean making fun of him for it. They talked about guys and girls, all their firsts, their best and their worst everything. 

“Wait. Jessica was your first?” Dean could see Sam trying to do the math. “But… That girl… What was her name? The dark haired one in...what? The seventh grade? Eight?”

“Michelle,” Benny supplied. “That was seventh grade we were in that friend group.” 

“Yeah. I mean. With her reputation and _your_ reputation, I thought for sure…” 

Dean shrugged. “Her reputation was because she refused some dude and he got pissed. Spread rumors. She got pissed at me when she found out they were the only reason I was hanging around her. But what did she expect from a thirteen year old guy?” Sam and Benny both shook their heads at him. “Hey. I learned my lesson, okay?” He caught the look Sam and Benny gave to each other and finished his beer in response. “Where’re we goin’, Sammy?” Dean hadn’t realized just how long they’d been driving. At least a couple of hours, he thought.

“You’ll see.” Dean didn’t trust the little smirk on Sam’s face when he said that. Especially when his baby brother handed him another beer. Dean took it anyway, of course, and sat back to drink it.

They finally turned off the highway, but Dean wasn’t paying enough attention to read the sign. It was about seven now, though, and he was starving. His stomach even loudly protested which made Sam laugh. “We have dinner reservations at eight."

The limo finally stopped and Dean got out to stretch, stopping with his arms midway above his head. A large, wood sign hung out over the hotel. “Buffalo Bill’s Irma Hotel” was carved into the wood and painted black. “No way.” Dean looked around to confirm his surroundings, breaking out into a wide grin. “This is awesome, Sammy!” Only his brother could put together a night in Dodge City on the fly like this.

He heard Sam laugh. “Wait ‘til you see the room.” That drew Dean’s grin wider across his face.

Sam was right. The room was awesome. It was a suite, really, with two bedrooms to share between the three of them. Dean was fine with that. They were full of warm colors and period pieces, and there was wood everywhere he looked. Old photographs filled the walls, each with a little description plaque. Dean went to each one to read it, until Sam nudged his shoulder and handed him his suit. “We have dinner reservations at eight. Get a move on, bottomless pit.” Dean opened his mouth to retort, but his stomach gurgled loudly, which caused Sam to guffaw. Dean stuck his tongue out instead and went to change.

★★★★

Dodge House Restaurant was _fancy_. At least, it was fancier than any place he’d ever been. Benny gave the hostess his name for the reservations, and that caused Dean’s eyebrow to raise a bit. “My pre-wedding gift to you, cher,” his friend explained with his own patented lopsided grin. 

Sam hadn’t just planned a fancy steak dinner for them. When they were done, he lead them to a casino. Sam shrugged when Dean asked about his reasoning. “I guess if I’d had more time I’d have planned a trip to Vegas or something with a stop over here.” Dean grinned and clapped his brother on the shoulder as the three of them made their way onto the casino floor.

The rest of the night was a blur. Dean drank way too much until way too late. He didn’t remember what time Sam and Benny poured him into his bed at the hotel, or them changing him into pajamas. Dean was grateful, though, when he woke up late the next morning for the aspirin and water set on the bedside table for him. 

“We have lunch reservations at twelve thirty.” That was Sam from the bed next to him. Dean groaned a little, wondering what time it was but not having the energy yet to find a clock. He let his head fall back onto the pillows while he waited for the aspirin to kick in.

It worked faster than he thought it would, and after a cup and a half of coffee, Dean was feeling more like himself. Sam assured him they wouldn’t have to dress up for the day, but that they should pack their bags to leave at the front desk. The limo would be back at seven thirty tonight, but they were checking out of the rooms. 

Sam had jam packed the day. “I wanted to get the most out of your bachelor party, jerk.” Dean grinned, and tried to reach up to mess up Sam’s hair, but Sam caught him and ducked away too quickly.

They ate lunch, and then went for beers at a beer bar. Dean was a little more careful with his drinking than he had been the night before. Being hungover for your wedding day wasn’t the ideal, even he knew that. He was glad, too, because when they walked out of the bar, Sam lead them to a little bus stop just outside of it. They weren’t there long enough for Dean to question his brother’s sanity because a little trolley pulled up then, and Sam nudged both Dean and Benny on board.

The tour was great. It went all around the historic town, stopping at points of interest. They could have gotten off and seen the sights more in depth, but this was good for Dean. He sat back and listened to the tour operator list off facts and trivia about the buildings, the streets, the town, and its past inhabitants. 

He took pictures, both of the scenery and of himself and Sam and Benny. Dean wasn’t usually a pictures kind of guy, but this felt important. Like he’d be sorry if he didn’t take the pictures, and so soon there was an entire album on his phone of pictures.

They got off the trolley near the middle of the town. It was only about four thirty, and Dean was curious about what Sam and Benny had planned for their last hours in Dodge City. There were a ton of people milling about the street, seeming to be watching for something. Dean looked around, too, but didn’t see anything of interest. 

“Let’s stand here a second. I need to get my bearings,” Sam told them. Dean was suspicious. Sam had known exactly where they were going this entire time. He let Sam and Benny come to a stop on the curb and he opened his mouth to say something, but before he could, he heard a horse (or horses) running toward them, and then a very enthusiastic _“YEE HAW!”_ rang out.

Dean perked up and turned toward the sounds, eyes bright. There were gunshots, and toward the end of the street he could see the pop of smoke that followed. The sound of hooves were coming from the opposite end now, and Dean’s head whipped toward them to watch the action. 

Two men in full getup galloped in on huge horses. Dean caught a glint of sun off of something from their chests. He squinted a bit, and as they rode closer he could see badges. Another taunting call echoed from down at the far end of the street as the two horses came to a stop nearly right in front of them. The actor sheriffs looked around, trying to figure out where the whooping was coming from. 

“The saloon,” one said. 

“The saloon? Why would he go there?”

“Chester’s his brother, ain’t he? He’d hide ‘im.”

“Naw. He’d shoot ‘im. Trapper ran off w’th Chester’s wife.” 

“Wasn’t that Chester’s sister?”

As they went back and forth a bit, movement caught Dean’s eye. He could see another person in period costume working his way toward the men on horses. The other man (presumably Trapper) was on foot and moving from cover to cover. 

_POP!_

The two men who were playing the sheriffs quickly climbed from their horses and took cover of their own, firing back toward Trapper. 

The gunfight lasted a few minutes, all three men moving around the street to different areas of cover while taking shots at each other. Dean knew it couldn’t last, or else the show would never end, so he was watching Trapper closely for his fatal mistake. Dean shook his head when he saw it, amused when the actor dropped “dead” in the street. 

He applauded with the rest of the crowd as the three men bowed and promoted giving donations toward the town’s historical fund, motioning to what looked like an old fashioned ballot box. “We also wanted to say ‘congratulations’ to Dean, who’s here for his bachelor party.” There was more applause, and Dean felt his cheeks warm in a way that had nothing to do with the sun. He glared at Sam, who gave him an innocent little smile that had always been able to get him out of trouble with his big brother. Shaking his head, Dean went up to it and tucked in some cash before turning back to Sam and Benny.

“That was _awesome_! Not just the show, even though that was the best part, but the whole thing. Thank you both.” 

“Not over yet, cher.” Dean gave them both a questioning look. He knew it wasn’t near seven thirty yet, but what else was there to do?

Sam gestured with a tilt of his head up the street a bit. “One more beer and dinner before we go.” Oh. Dean realized he was hungry only when Sam suggested food and he nodded as they started to walk toward Dodge City Brewing.

The limo was right on time, and Dean even fell asleep on the way back to Lawrence. He didn’t unpack when they got home after dropping Benny off, but he didn’t go to bed, either. The nap had energized him just enough for the realization of tomorrow to hit. All of the same questions he’d thought about when Pam had first called to tell him she’d found him a match swirled again, interspersed with questions about the ceremony and reception. What had Tessa come up with? Was it something he was going to like? Would he even notice any of it with how bad his nerves were? 

Dean spent a couple of hours pacing the house, unable to sit still as his brain jumped from one question to the next with exactly zero answers for any of them. 

“Dude, I can hear you thinking.” Dean jumped, not realizing Sam had come up behind him. 

“Sorry.” His brother shook his head and held his freakishly large hand out, half of a small circular pill sitting in the center. 

“Take it. It’ll help you rest and it won’t make you feel hungover tomorrow.” When Dean hesitated for another minute, Sam took Dean’s hand in his own and dropped the pill into it. “Take it. Trust me.” When had the tables turned so that Sam was now taking care of him? Dean swallowed the pill dry and let Sam lead him back to his room. Dean actually got into the bed this time, eventually drifting off into sleep.


	8. The Officiant

**Summary for the Chapter:**

> Where Dean gets married.

His alarm went off way too early if you asked Dean. But the moment it did, he was wide awake and on the verge of panicking again. He laid in bed fighting the worst of it, knowing he wouldn’t want to be worked up like that when it came time for the ceremony. He went through breathing techniques to keep himself from completely freaking out, waiting until he could go at least two full minutes without the panic starting to rise up in his chest again. When he got to that point, Dean climbed out of bed.

It was nine and the ceremony was at one. He had to eat and get dressed and head to the ceremony location which was only twenty minutes away. He had time, which made him more nervous while also calming him that he wasn’t in a rush. Dean knew he was an emotional mess. Coffee would help. He made a beeline for the Keurig and started a cup to brew.

He figured he should probably eat, too. While the coffee brewed, Dean rummaged through the fridge to find something suitable for breakfast. He pulled out bacon and potatoes to fry up along with a couple of eggs. Realizing he hadn’t seen Sam yet, Dean took out the whole carton and a pepper that Sam must have brought with him that was in the fridge. 

Dean lost himself in making breakfast. It was a simple task that he generally enjoyed for himself and it was a familiar one that he’d done thousands of times for Sam when they were kids. Bacon first for the grease, and when it was done he threw it in the oven to keep warm before tossing the seasoned potatoes into the pan to fry.

He set to putzing around the kitchen. His mind did wander, but he fought against the anxiety that came with the thoughts as best he could. He tried to push up the excitement that was bubbling underneath that anxiety. This was a new, very crazy, adventure and he liked adventures. 

“Morning.” 

Sam shuffled in behind Dean, reaching across him for his own cup of coffee. His brother leaned against the counter as he sipped it, watching as Dean finished cooking their breakfast. “Take a picture, Sammy.”

“Just tryin’ to see if you’re gonna freak out on me.” 

Dean didn’t answer Sam right away. He wasn’t sure how to because a panic attack was still a clear possibility. He could feel it bubbling just below the surface but pushed it away again, harder this time. “I’m fine, Sammy,” he finally told him, plating their breakfasts. 

★★★★

Now that he was at the church, he wasn’t as able to control the panic. He was getting  _ married _ . That was what caused most of the anxiety, really. 

Someone knocked, and either Bobby or Sam opened the door. “Dean?” Tessa waved a hand in front of his face, pulling him back from the edge of his panic a bit. “Doing okay? Can I get you anything?”

“What? No. I mean, yeah I’m alright and no I don’t need anything.” Jesus, he hoped he wasn’t such a spazz when it came time to talk to his… Whoever he was marrying. 

She smiled at him, that reassuring one that she was good at. “You’re going to walk down first, with Sam. And then your match with their… Sam.” Dean had to chuckle at how hard everyone was working to keep his match’s gender from him. “The officiant - Billie - is already up there. She’ll introduce herself to you before your match starts down the aisle, and then to your match once they’re up front, too. Do you have your vows?”

Absolute terror hit Dean in the chest. Vows?  _ Vows!?  _ No one had said anything about vows! What was he supposed to write to a complete stranger? Was he the one who was promising to obey, or was his match? What if-

Sam shoved a piece of paper at him. “Deep breath, jerk. I knew you would spend the last few days panicking if you had to write it so…” Sam shrugged as Dean’s shaking hand took the folded paper and opened it to read. 

It was perfect, because of course Sam had written something perfect for him. “Tha--” His voice cracked and Dean cleared his throat. “Thanks, Sammy.” 

“Well,” Tessa broke in, “that’s it, then. Ready?”

“Now?” Dean’s head snapped up to look at her, eyes wide and mouth dry. She nodded. Then Dean nodded, but didn’t move. He closed his eyes and took a deep breath to try to calm his racing heart. Dean tucked the paper with the vows into his inside breast pocket, took one more deep breath, and then nodded again.

“I’m ready.”

The walk down the aisle was surreal. The last few weeks played back in his head, he didn’t even pay close attention to the faces in the chairs. It didn’t occur to him to try and read hints from the people he didn’t know. 

“Hi Dean.” How had he made it up to the front of the aisle without realizing it? “I’m Billie. It’s nice to meet you, and congratulations.” She smiled at him, and his response was automatic. He knew she could read his nerves in the half smile he returned but he couldn’t pull himself together enough to correct it.

Music played. Had music played while he and Sam walked down the aisle? Dean had his back to where his match would come in and he was terrified to turn around. What if she wasn’t his type? Or what if he didn’t like Dean? Dean felt Sam nudge his shoulder, bringing him out of that circular thinking. He turned and looked up, and as soon as he did his breath caught in his throat. 

He  _ knew  _ him. Well. One of them. The blond had been his candy-loving hook-up from months ago, and Dean felt his jaw drop a little. He saw recognition in the blond’s eyes, and he swore the little sigh of relief was not at the subtle shake of the blond’s head. Dean focused on the other man walking with him. Gorgeous didn’t quite cover it. Strong jawed and blue eyes that he could see from halfway down the aisle. He looked just as nervous as Dean was, but much more observant. His match’s eyes darted around, seeming to take in everything he could. 

Dean continued to stare as Billie introduced herself to him, so enthralled he missed his name the first time she said it.

“Dean, meet Castiel. Castiel, meet Dean.” 

Dean had no words, but he felt a bit of a goofy-nervous smile play at the corners of his lips. 

“Hello, Dean.” His voice was gravel blended with liquid sex. Dean could literally feel his knees go weak. The blue suit that Castiel wore complimented his eyes, though the grey suit would have, too. Shit. He was one of those people who looked good in anything and would make Dean’s jeans and t-shirts look raggedy. 

Finally, Dean managed words. “Heya Cas.” That earned him an odd look and Dean bit his lip, wondering if he’d crossed a line already.

Billie started the ceremony, then, drawing Dean’s attention. “Dean, Castiel’s friends and family would like you to know that he is a passionate and loyal person, and they’re hoping that you will find his quirks endearing.

“Castiel, Dean’s friends and family would like to warn you about his tendency to turn every situation into a movie quote, his superior cooking skills, and that he is one of the hardest working people they know.”

When had they said that about him? Dean wanted to look over to Sam, but he couldn’t quite find the strength to look away from Castiel’s gaze.

“Castiel, do you have your vows?”

His match -  _ fiance  _ \- reached into his pocket to pull out a square of paper nearly identical to the one Sam had handed him. “Dean, I promise to work hard to get to know you, and grow to love you. I promise to work equally to build a life together and to be the balance in your life. I promise to support you in your ventures, and in your times of need. I promise to offer strength when you need it, and to offer friendship always.”

There was a stretch of silence that seemed to last forever as Dean absorbed these words. They were big promises for someone who’d never met him before. Did Castiel write them? Or did… What was his name? Blondie, the way Sam had for him? Sam nudged him again, and Dean realized the silence was because they were waiting for him. Oh.

“Castiel,” Dean was sure to pronounce his full name since he’d acted so oddly at Dean’s shortening of it. “I promise you laughter, and a soft place to land. I promise loving support in an equal partnership that we build together. I promise to listen without judgment, I promise to support without question, and I promise to love without reservation.”

Dean heard sniffling and couldn’t make out who it was. His bet was on Bobby who would blame it on Ellen, but there were ten people there who he didn’t know at all and  _ all _ of them could be crying for all he knew.

Billie asked for their rings and Dean’s heart stopped. He hadn’t picked up the ring box! It had been right there on the counter, he could  _ see it _ in his mind and he knew he hadn’t taken it! But Sam, his wonderful brother who he would owe for the rest of his life, was handing him the familiar black box over his shoulder. “What is your best man for?” he whispered with a grin.

“Castiel, do you take Dean to be your husband?”

“I do.” Cool metal slid onto his finger. It felt heavy, but right. Dean wondered for only a second how it could feel so right so quickly, but then Billie was asking him if he took Castiel to be his husband. 

“I do.” Dean lifted Castiel’s hand. His skin was warm and dry, and it felt perfectly (there was that word again!) heavy in his hand. He slid the ring onto Castiel’s left ring finger.

“I pronounce you married. You may kiss.”

Kiss. Dean hadn’t thought about kissing. 

Kiss? They hadn’t spoken to each other beyond their vows! 

He could see a blush in Cas’s cheeks, and Dean could feel it in his. Taking the bull by the horns, he leaned forward, bending just so. They were nearly the same height, and brushing a soft kiss to Castiel’s warmed cheek was easy. And damn did he smell good, too. If he wasn’t sure of it before, Dean was sure now that he was in for the ride of his life with this Castiel. 

Vaguely, Dean heard the light applause. It was probably Bobby who whistled. Or maybe the red head he’d spotted but not recognized. She looked like a firecracker. 

He stood up straight then and turned to face the guests, feeling Castiel lace their fingers together like they’d been doing it for years. He felt his match -  _ his husband _ \- squeeze his hand, and Castiel was the first of them to take a step off of the little stage area where they were standing to head out of the spotlight. Dean was grateful for that, and he squeezed back, giving Castiel a little grin.

As they walked back down the aisle, Dean really took in the sight now. It was very small. The garden they were in barely fit the twenty four of them, but it was beautiful. Flowers covered nearly every free inch of land, other than where the chairs had been set up on either side of the aisle. He had no clue what they were, but the smell was intoxicating. There was a rope of flowers that were hung along the inside chairs, and rose petals covered the light sage runner that marked the aisle they had walked down. It was warm and sunny and perfect, and Dean couldn’t have put something like this together if he’d tried. 

He was married. He wondered if his new husband was feeling the same amount of wonder that he himself was feeling. Dean wasn’t ready to break the silence yet, even as they walked out of view of the little ceremony. He just needed a few more minutes before he actually spoke to Castiel; a few more minutes before this all  _ really _ became real.


	9. The Match

**Summary for the Chapter:**

> Where Dean actually speaks to his husband.

Tessa had set up a quiet area for them to talk. There were two comfortable looking chairs angled in and facing each other, bottles of water and a platter of fruit for them to pick on with a note card laid out beside the platter. Their names were written elegantly (in Dean’s opinion) on the front of the card. Dean opened and read it:

**_Dean & Castiel,_ **

**_Pam and I hope that you find this space comfortable enough to begin to open up to each other and build on the profound bond we both think you’ll come to have with each other. Entertainment for your families and friends has been arranged for the next few hours. We’ve included some ice-breaker questions for you, just in case you get stuck. Someone will be by to let you know when it’s time to go to your reception._ **

**_We wish you the very best of successes and a long, happy marriage._ **

**_Pamela Barnes and Tessa McKeon_ **

He shook his head and handed the note over to Castiel to read. There were strips of paper in the envelope, folded. Each one had one of their names written on it. Dean took his out of the envelope and handed that to Castiel too. 

Dean stood there, chewing his bottom lip and trying to figure out how he should act. Should he sit? Open water for both of them? What if Castiel didn’t want water? Was he still mad that he’d called him “Cas” earlier? Castiel sat, though, and so Dean followed suit, because who wanted to have anyone towering over them while they sat down?

He watched Castiel smile at the note, fold it, and return it to the envelope after removing his own strips of paper. “Hello, Dean,” he repeated in his same still-wrecked-after-being-thoroughly-fucked voice. It sent a shiver down Dean’s spine in the most delicious sort of way. 

“Hey. I didn’t mean to upset you earlier.” The head tilt was adorable. Seriously. How could one person be that sexy  _ and  _ adorable at the same time? “With shortening your name, I mean.”

His husband’s eyes went a little wide. “I- No, you didn’t upset me. It just… Well, no one’s ever called me that before.” Dean felt his jaw drop a little. With a name like Castiel, it was just natural to shorten it he felt. “I kind of liked it, actually.” Dean ducked his head a bit, trying to hide the little smile that was pulling at his lips. He liked that Castiel - Cas - liked the nickname. “What do you do, Dean?” He also liked the way Cas said his name.

“I own an auto shop. Baby’s. It’s right in town.” He watched as Cas’s eyes grew a little wider. Dean chuckled and rubbed the back of his neck. “I take it you’ve heard of us?” He was always so grateful that the shop took off the way it did. It allowed him to live a nice life, but he was always a little uncomfortable with the knowledge that people usually knew about the shop before he even told them about it.

Cas nodded. “I have an older car and Gabriel-”

“That’s his name!” Dean realized he said that outloud and bit his lip. “Sorry. Go ahead.” He literally watched Castiel file a question away in his brain and he cursed to himself.

“Gabriel, my brother, told me to bring my car there. To your shop, I mean. Do you know Gabriel?”

Fuck. He’d hoped for a little more time before he had to answer that question. Dean fidgeted with the paper in his hand, playing with the corner of it until it nearly disintegrated before he actually spoke. “I spent a lot of years in bars and clubs,” he finally answered. “Gabriel was there one night and…” He shrugged, figuring Cas would stand and demand an annulment right then and there. 

As it was, Cas was quiet for what felt like a long time after. Dean opened his mouth to say he’d leave and let Pam know it didn’t work, but Cas spoke first. “It’s not something anyone could have predicted, I suppose. Lawrence is small, compared to some place like Kansas City. I can’t fault you for having a past, Dean.”

Dean let out a breath that he didn’t know he was holding. 

“We have a lot to learn about each other. Maybe setting some boundaries will help us better navigate?” Cas suggested.

“What do you mean?”

Cas seemed to think for a moment, and then he spoke. “Things like leaving our pasts in the past when it comes to partners. And if there are subjects we’d like to be off limits, at least for the time being, we can set that, too.”

“I, uh… I don’t have anything else that I’m em.. That I’m not open to talking about.” Dean stumbled over his words a bit, not wanting to admit embarrassment at his behavior in his very recent past. Cas just smiled at him, and not one of those condescending ones that most people did. It made him feel better; it made him feel less like a fuck-up.

“I don’t, either,” Cas agreed. He looked relaxed in his chair, leaning back just enough to not look apathetic. It helped to put Dean at ease. 

“What is it that you do, Cas?” 

Was that a blush in Cas’s cheeks? “Oh, I’m a florist. I own my own shop, The Busy Bee.” 

“The Busy Bee?”

Cas ducked his head a touch. “Yes, I’m, um. Quite the bee enthusiast. And I didn’t have the space to keep bees myself so I figured I’d grow their food for them.” Dean thought that was adorable. 

“Who stood with you?” Dean must have looked confused because Cas clarified, “Today at the altar?”

“Oh. That’s my little brother Sam. I’ve practically raised him his whole life. Are you older or younger than Gabriel?”

“Younger, but most people assume I’m older. He’s more… Carefree, I guess.” Dean managed to hold in a snort at that, because “carefree” was definitely an apt description of Gabriel. 

The more they spoke, the more at ease Dean was. He felt himself relaxing into the chair beneath him more, realizing for the first time that it was actually comfortable. They traded nightmare customer stories, Cas telling him about the dreaded five o’clock Valentine’s rush while Dean told him about a time a family wanted the oil changed on their car. “They stopped in, literally, on their way out of town for a roadtrip to California. Normally it’s no big, right?” Dean loved the little nod Cas gave him as he was sitting forward in his chair, obviously paying great attention to his story. “Except that this car had probably never had its oil changed in its life! It was like tar! The woman blew her top, screaming and hollering like it was  _ my _ fault she didn’t take care of her car or somethin’, and then expected all that work to be free!”   
  
“No she didn’t!”

“Hand to God.” Dean raised his hand, not that he believed in God, really. “When I laughed she demanded the manager.”   
  
“Did she get mad when you told her you were the owner?”

“Nah,” Dean shook his head with a little smirk. “I let Benny talk to her. When he told her the same as me, she insisted that she knew the owner and she was gonna call  _ her _ right then. She blew her gasket when I called over asking if she had my new phone number. Outright pterodactyl shrieked and stormed out of the garage.” 

Cas was laughing, and it was a good look on him. His eyes crinkled at the corners, lighting up his entire  _ being _ ; it lit up the entire room and it made Dean’s chest warm. “What? Is there something on my face?”   
  
Dean blinked, eyes coming into focus again. “Huh?” Cas chuckled before telling him he was staring. “Oh.” Dean felt his cheeks color lightly and he ducked his head for a second. “Sorry. Just. Your smile is really great.”

The color that came up into the apples of Cas’s cheeks was lovely, too. “Thank you, Dean. I find that your smile is...infectious. Tell me who was here to support you?”

Dean hesitated a bit, wondering how far into his childhood to go. He wound up dancing around it a bit, simply saying that it wasn’t the best and that Bobby and Ellen were his and Sam’s defacto parents, thus making Jo and Ash their siblings...somehow. They were never really sure how Ash figured in, he showed up at the Roadhouse and stayed one day, and that was that. “Jody got us out of a tough spot when we were young, s’how we wound up with Bobby and Ellen full time. Donna’s another sheriff. Those two have been together for a long time.” 

He had a hard time explaining Garth and how they became friends, because by all rights they probably shouldn’t have been with how opposite they were. “But Garth, man. He just loves everyone with his whole heart, and so you love him right back,” he finally said with a shrug. “Bess is his wife, real religious girl with a nice enough family. Perfect for Garth, you know?”

“And Benny is your right hand man,” Cas finished for him with a soft smile. 

“Yeah. Grew up together once we settled at Bobby’s. Got into trouble together and pulled our shit together at the same time. Through thick and thin with him, you know? He was always there, didn’t matter what for or when or anything. No questions kind of guy, just fierce and loyal.”

“It sounds like you have some really great people around you.”

Dean nodded, realizing once more just how truly blessed he was. “What about you? Who’s here for you?”

“Well you know Gabriel,” Cas teased lightly, making Dean laugh a little. Then Cas told him about the fiery redhead he’d seen sitting across from his family named Charlie and her wife Dorothy. His parents were Naomi and Chuck, but they split up a while ago and Chuck was dating Becky. He told him about his two other siblings Samandriel and Anna, both younger than him by a lot. “We’re not very close, really. We get along well enough, but it’s not the same as me and Gabe.”

“The age difference was too much?” Cas shrugged a bit.

“I think so. When you’re in high school and they’re just starting second and third grade… You don’t have a lot in common even then. There’s nothing there to build a foundation of friendship the way there was for me and Gabe. And Alfie and I -”

“Alfie?”

“Samandriel. It’s a mouthful but Mother insisted so we had to find  _ something _ that was better.” Dean barked out a little laugh and shook his head a bit. 

“Poor kid.”

“Which is why he doesn’t complain about Alfie. He knows how much worse he could have had it. And that leaves Meg and Jack. Meg and I have been friends since middle school. She’s abrasive. She’ll want to interrogate you. And Jack… Well, Gabe and I kind of adopted him in our senior year of high school, I guess. His mom had died and he didn’t have anyone… He was only in the eighth grade and needed… guidance, I guess.”

Cas talked more about Jack, and Dean could see pride shining in his eyes. He knew the look, because he had it every time he spoke about Sam. 

They drifted through conversations, sometimes using one of the questions that Pam and Tessa had given to them just for something new or different. The conversation never once felt forced, and Dean found himself hanging on every word that Cas said. 

Dean pulled the last strip of paper out of his pile and read it out loud. “Read your ring inscriptions and give your husband an explanation of why you chose it.” Dean smiled and blushed at the same time, but pulled his ring off and read the inscription from the inside of it. “Hope is the only bee that makes honey without flowers.” He looked up to Cas as he slid his ring back on.

“It’s one of my favorite quotes, by Robert Green Ingersoll. It just… It put everything I was feeling into ten little words. Hoping that we will be able to build something beautiful together.” 

“I think we will,” Dean answered as Cas slid his ring off and read the inscription.

“Swoon. I’ll catch you.” When Castiel looked up at him, an eyebrow was raised. Dean grinned at him.

“I didn’t know what to pick. I spent like. An entire weekend pouring through chick flicks, looking for something like you said. That put everything I was feeling into words. But… I don’t think that one thing exists, you know? And that line… I mean. It’s just something I’d say and so I figured that made it more perfect than some sappy quote that didn’t click with me.” 

“I love it, Dean,” Cas told him. “I think it’s absolutely perfect.” Those words made Dean’s heart swell a little.

He didn’t even see someone he didn’t know approach them. “Gentlemen? Tessa sent me to let you know that you’re expected at your reception in ten minutes.”

Dean took a deep breath. “Ready, Cas?” he asked as he stood. Dean hesitated for a minute before holding his hand out in offer to Castiel. Cas took it without hesitation as he stood.

“Ready.”


End file.
